Synthesis of a naturally occurring diene-containing amino acid and its glutamyl dipeptide via N-acyliminium ion chemistry

European Journal of Organic Chemistry

Volumn , Issue 5, 2008, Pages 914-924

  Berkheij, Martin ^a   Dijkink, Jan ^a   David, Olivier R P ^b   Sonke, Theo ^c   Ijzendoorn, Denis R ^d   Blaauw, Richard H ^d   Van Maarseveen, Jan H ^a   Schoemaker, Hans E ^a,c   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^c DSM Pharmaceutical Products   (Netherlands)

^d CHIRALIX B V   (Netherlands)

Author keywords

Allylsilanes; Dienes; Enzymatic resolutions; Natural products; Peptides

Indexed keywords

EID: 53649106024     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701016     Document Type: Article

References (27)

1. L. Campos, M. Marlier, G. Dardenne, J. Casimir, Phytochemistry 1983, 22, 2507-2508.
2. D. O. Gray, L. Fowden, Phytochemistry 1972, 11, 745-750.
3. L. Fowden, H. M. Pratt, A. Smith, Phytochemistry 1972, 11, 3521-3523.
4. L. Fowden, J. W. Anderson, A. Smith, Phytochemistry 1970, 9, 2349-2357.
5. M.-L. Sung, L. Fowden, D. S. Millington, R. C. Sheppard, Phytochemistry 1969, 8, 1227-1233.
6. E. V. Ellington, C. H. Hassall, J. R. Plimmer, C. E. Seaforth, J. Chem. Soc. 1959, 80.
7. G. A. Rosenthal, Plant Nonprotein Amino and Imino Acids, Academic Press, New York, 1982.
8. S. Kotha, K. Mandal, S. Banerjee, S. M. Mobin, Eur. J. Org. Chem. 2007, 1244-1255.
9. R. Chen, V. Lee, R. Adlington, J. Baldwin, Synthesis 2007, 113-117.
10. B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431.
11. W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817-3856.
12. E. C. Roos, M. C. Lopez, M. A. Brook, H. Hiemstra, W. N. Speckamp, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1993, 58, 3259-3268.
13. H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, Tetrahedron 1989, 45, 4627-4636.
14. G. Mentink, J. H. Van Maarseveen, H. Hiemstra, Org. Lett. 2002, 4, 3497.
15. W. J. N. Meester, J. H. Van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2003, 2519-2529.
16. P. H. Lee, K. Bang, H. Ahn, K. Lee, Bull. Korean Chem. Soc. 2001, 22, 1385-1389.
17. From a short literature survey, TMSI-induced diene degradation can be excluded as another possible reason.
18. In another experiment we also have observed polymerization. Solid products are relatively stable; when the product was isolated as an oil, polymerization occurred overnight, even when the compound was stored under nitrogen. When stored in solution, the compounds proved to be stable, even after prolonged storage times.
19. T. Sonke, B. Kaptein, W. H. J. Boesten, Q. B. Broxterman, J. Kamphuis, F. Formaggio, C. Toniolo, F. P. J. T. Rutjes, H. E. Schoemaker, R. N. Patel, Stereoselective Biocatalysis, Marcel Dekker, New York, 2000, chapter 2, p. 23-58.
20. S.-T. Chen, S.-T. Chen, S.-C. Hsiao, K.-T. Wang, Biotech. Lett. 1991, 13, 773-778.
21. S.-T. Chen, K.-T. Wang, C.-H. Wong, J. Chem. Soc. Chem. Commun. 1986, 1514-1516.
22. J. M. M. Boesten, M. Berkheij, H. E. Schoemaker, H. Hiemstra, A. L. L. Duchateau, J. Chromatogr., A 2006, 1108, 26-30.
23. L. B. Wolf, T. Sonke, K. C. M. F. Tjen, B. Kaptein, Q. B. Broxterman, H. E. Schoemaker, F. P. J. T. Rutjes, Adv. Synth. Catal. 2001, 343, 662-674.
24. D. M. Shendage, R. Frölich, G. Haufe, Org. Lett. 2004, 6, 3675-3678.
25. F. P. J. T. Rutjes, J. J. N. Veerman, W. J. N. Meester, H. Hiemstra, H. E. Schoemaker, Eur. J. Org. Chem. 1999, 1127-1135.
26. Z. Bernstein, D. Ben-Ishai, Tetrahedron 1977, 33, 881-883.
27. Shifts and coupling constants are concentration-dependant.